Lithium Bromide → HCID 59526939, compound

HRID 384437Notes

Reaction equation

HRID 384437 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:19]Cl)[C:10]=1[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-:22].[Li+]>C1COCC1>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:19][Br:22])[C:10]=1[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 108278984-(Benzyloxy)-2-(chloromethyl)-3-methylquinoline

Product 1

HCID 59526939HCID 59526939, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(benzyloxy)-2-(chloromethyl)-3-methylquinoline (5.0 g) in THF (50 mL) was added anhydrous lithium bromide (15 g), followed by heating under reflux for 3 hours. The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. Water was added to the residue, followed by stirring, and the resulting solid was collected by filtration. This solid was dried under vacuum at 60° C. to obtain 5.73 g of 4-(benzyloxy)-2-(bromomethyl)-3-methylquinoline as a white solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 3 hours
  3. customthe solvent was evaporated under reduced pressure
  4. additionWater was added to the residue
  5. filtrationthe resulting solid was collected by filtration
  6. customThis solid was dried under vacuum at 60° C.

Sources & evidence

ORD record
ord-b5f8e900a3d448d694134248d658bc9c
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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